A modified backbone amide linker (BAL) solid-phase peptide synthesis strategy accommodating prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus

Author:

Alsina Jordi,Yokum T.Scott,Albericio Fernando,Barany George

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference19 articles.

1. Abbreviations used: BAL, Backbone Amide Linker, (Ref. 6), specifically as implemented in the tris(alkoxy)benzylamide system; DIPCDI, N,N′-diisopropylcarbodiimide; HATU, N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate N-oxide; HOBt, 1-hydroxybenzotriazole; IRAA, ‘internal reference’ amino acid; NMM, N-methylmorpholine; o,p-PALdehyde, 4-[(4 or 2)-formyl-3,5-dimethoxyphenoxy]butyric acid; PyBOP, benzotriazol-1-yl-N-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate.

2. (a) Lloyd-Williams, P.; Albericio, F.; Giralt, E. Chemical Approaches to the Synthesis of Peptides and Proteins; CRC: Boca Raton, FL, 1997; (b) Fmoc Solid Phase Peptide Synthesis, A Practical Approach; Chan, W. C.; White, P. D., Eds.; Oxford University Press: Oxford, UK, 2000. (c) Fields, G. B.; Lauer-Fields, J. L.; Liu, R.; Barany, G. In Synthetic Peptides: A User's Guide; Grant, G.A., Ed.; 2nd Edition, Oxford University Press: New York, 2000, in press.

3. Atherton, E.; Benoiton, N. L.; Brown, E.; Sheppard, R. C.; Williams, B. J. J. Chem. Soc. Chem. Commun., 1981, 336–337.

4. Sieber, P.; Riniker, B. Tetrahedron Lett. 1987, 28, 6031–6034.

5. Barlos, K.; Chatzi, O.; Gatos, D.; Stavropoulos, G. Int. J. Peptide Protein Res. 1991, 37, 513–520.

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